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1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in N,N-dimethyl-formamide T=20°C;

hydroxylamine hydrochloride; sodium acetate; toluene-2-sulfonic acid in ethanol; water; acetic acid

1: 60 percent / SOCl2 / CH2Cl2 / 3 h / Heating 2: 1) triethylamine / 1) methylene chloride, 30 min, reflux, 2) methylene chloride, 30 min, reflux 3: 63 percent / CHCl3 / 2 h / Ambient temperature View Scheme

1: 90 percent / triethylamine / toluene / 2 h / Heating 2: 60 percent / SOCl2 / CH2Cl2 / 3 h / Heating 3: 1) triethylamine / 1) methylene chloride, 30 min, reflux, 2) methylene chloride, 30 min, reflux 4: 63 percent / CHCl3 / 2 h / Ambient temperature View Scheme

1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in acetone 12 h; Inert atmosphereReflux;